DE10036956A1 - Amides of hydrocarbylamines and use of these amides - Google Patents

Abstract

The invention relates to novel compounds of general formula (I): R<1>R<2>NR<3>, wherein R<1> represents C31-C400 alkyl or C31-C400 alkenyl group, a C8-C400 alkyl aryl or a C8-C400 alkenyl aryl group; R<2> represents H, C1-C18 alkyl, C2-C18 alkenyl, C4-C18 cycloalkyl, C1-C18 alkyl aryl, C2-C18 alkenyl aryl, hydroxy C1-C18 alkyl, a poly(oxyalkyl) radical, a polyalkylene polyamine radical or a polyalkylenimine radical; R<1> and R<2>, optionally from a hetrocyclic ring comprising 6 - 400 carbonic atoms with the nitrogen atom to which they are bonded; and R<3> represents an acyl radical of a mono- or polycarbon acid, and includes at least one free hydroxy- and/or amino group, wherein the amino group includes, optionally at least one hydroxy C1-C4 alkyl group. The invention also relates to the use of said compounds as a power or lubricant additive or as an anticorrosion agent in aqueous liquids.

Description

The present invention relates to novel hydrocar amides bylamines, which are used in particular as emulsifiers for water-in-oil Emulsions are suitable. The invention also provides the use of such amides as an additive for power and lubrication substances and for the production of liquid explosives subsidence. Further objects of the invention relate to power and Lubricant compositions and fuel additive packages, wel che contain such amides and processes for their preparation such amides.

Compounds of different types are known from the prior art known with emulsifying or dispersing properties. So describes for example, US-A-4,225,447 water-in-oil emulsions, which a polyalkenyl succinic anhydride or a polyalkenyl berber include succinic acid as an emulsifier. From GB-A-2,157,744 Drilling fluids known as dispersants Polyisobu tylenesuccinic anhydride can contain. EP-A-0 156 572 describes the use of polyisobutenyl succinic acid derivatives for the production of water-in-oil or oil-in-water emulsions NEN.

From US-A-4,512,903 there are friction reducing additives for Lubricants are known, which are accessible by implementing egg ner hydroxy-substituted aliphatic monocarboxylic acid chooses from glycolic acid, lactic acid and 2,2-bis (hydroxyme thyl) propionic acid, with an amine of the formula RR'NH, where R is an aliphatic hydrocarbyl group with 10 to 30 carbon atoms men and R 'for hydrogen or an alkyl group having 12 to 18 Carbon atoms.

US Pat. No. 5,858,029 describes friction-reducing additives for fuels and lubricants, compounds of the formula R ¹ (OR ² ) _a NHCOR ³ OH, in which R ^{1 represents} a C ₁ -C ₆₀ -alkyl radical, are used in particular as friction-reducing additives , R ^{2 is} a C ₁ -C ₄ alkylene radical, a is an integer from 1 to 12 and R ^{3 is} C ₁ -C ₄ alkylene or substituted alkylene or cycloalkyl.

Liquid explosives usually comprise aqueous emulsions of an inorganic oxidizing agent, such as e.g. B. ammonium nitrate, in egg ner water-immiscible organic phase. According to the prior art, emulsifiers of various types are used to produce such emulsions. For example, US-A-5,639,988 and US-A-5,460,670 describe the use of special hydrocarbyl polyamides as emulsifiers. US-A-4,356,044 and US-A-4,322,258 describe the use of sorbitan fatty acid esters, glycerol esters, substituted oxazolines, alkylamines and salts and derivatives thereof as emulsifiers for this purpose. US-A-3,447,978 proposes the use of various sorbitan fatty acid esters and various fatty acid glycerides as emulsifiers for liquid explosives. From US-A-4,141,767 the use of C ₁₄ -C ₂₂ fatty acid mines or ammonium salts as emulsifiers for explosives compositions is known. WO 96/41781 describes emulsifier compositions which contain, as the main component, an alkylcarboxylic acid mid, alkenylcarboxamide, poly (alkylene amine) or a (di) alkanolamine of a special structure as the main component. The emulsifier systems are suitable for the production of explosive emulsions. GB-A-2,187,182 describes explosive compositions comprising, as emulsifier, a poly [alk (en) yl] succinic acid or a derivative thereof. From WO-A-88/03522 nitrogenous emulsifiers are known for the manufacture of explosive compositions, which are derived from a carboxylic acylating agent, at least one polyamine and at least one acid or an acid-producing compound which are used to form a salt with the polyamine is capable.

For the production of water-in-oil emulsions for liquids Explosives today are mainly used as emulsifiers amide Derivatives of polyisobutylene succinic anhydride used. These have the disadvantage that they can only be obtained through complex syn these are accessible. In addition, in the synthesis fall in high proportion and in varying amounts of by-products the setting of a constant product quality, such as B. a constant viscosity of the emulsifier is difficult. Corresponding disadvantages result from the manufacture the explosives emulsion.

The sub-known in the above, known from the prior art However, stamps indicate with regard to manufacture and / or product various disadvantages.

The present invention was therefore based on the object to provide amides which are those from the prior art no longer have known disadvantages. For example, should  the novel connections are easier to produce and the same che or improved emulsifying properties. Moreover the connections should be applicable in a variety of ways.

Surprisingly, the above object was achieved by providing compounds of the general formula I

R ¹ R ² NR ³ (I)

wherein
R ^{1 represents} a C ₃₁ -C ₄₀₀ alkyl or C ₃₁ -C ₄₀₀ alkenyl group, a C ₈ -C ₄₀₀ alkyl aryl or a C ₈ -C ₄₀₀ alkenyl aryl group;
R ^{2 is} H, C ₁ -C ₁₈ alkyl, C ₂ -C ₁₈ alkenyl, C ₄ -C ₁₈ cycloalkyl, C ₁ -C ₁₈ alkyl aryl, C ₂ -C ₁₈ alkenyl aryl, hydroxy -C ₁ -C ₁₈ alkyl, a poly (oxyalkyl) -, polyalkylenepolyamine or polyalkylene niminrest;
R ¹ and R ² together with the nitrogen atom to which they are attached optionally form a heterocyclic ring having 6 to 400 carbon atoms; and
R ^{3 stands} for an acyl residue of a mono- or polycarboxylic acid, and carries at least one free hydroxy and / or amino group, the amino group optionally carrying at least one hydroxy-C ₁ -C ₄ -alkyl group.

In particular, in compounds of the formula I, the radical R ^{3 represents} an acyl radical of the formula (C = O) R ⁴ , in which R ^{4 is} selected from C ₁ -C ₁₈ alkyl, C ₂ -C ₁₈ alkenyl, C ₄ -C ₁₈ cycloalkyl, C ₁ -C ₁₈ alkyl aryl or C ₂ -C ₁₈ alkenyl aryl radicals which carry at least one hydroxyl group and / or amino group, and the analogs of these groups which carry at least one further carboxy group.

In a further preferred embodiment, compounds of the formula I are provided in which R ^{1 is derived} from a poly-C ₂ -C ₆ -alkene, and in particular from monomers selected from ethylene, propylene, 1-butylene, 2-butylene, i- Butylene or mixtures thereof, is built up. The poly-C ₂ -C ₆ -alkene is preferably a reactive poly-C ₂ -C ₆ -alkene with a high proportion of terminal Vi nylidengruppen.

In a particularly preferred group of compounds of the formula I, R ^{1 represents} a C ₃₁ -C ₄₀₀ alkyl or alkenyl group; R ² for H; and R ³ for an acyl residue of a mono- or polycarboxylic acid, preferably selected from glyceric acid, gluconic acid, lactic acid and glutamic acid.

The invention further relates to water-in-fuel emulsions which are characterized in that they contain as emulsifier at least one compound of the formula I in a proportion of about 1 to 20% by weight, based on the total weight of the composition , where R ¹ in compounds of the formula I can also represent a C ₆ -C ₃₀ alkyl or alkenyl group; where appropriate, the emulsifiers according to the invention are used in combination with at least one further customary emulsifier.

Preferred are also water-in-fuel emulsions characterized that they have about 60 to 95 wt .-% fuel and contain about 3 to 35 wt .-% water.

The invention further relates to liquid explosive compositions which comprise at least one compound of the formula I as defined above, optionally in combination with at least one further customary emulsifier, as an emulsifier for a water-in-oil or oil-in-water emulsion. Here, R ¹ in compounds of the formula I can also represent a C ₆ -C ₃₀ alkyl or alkenyl group.

A preferred group of liquid explosive compositions includes:

• a) 0.5 to 20% by weight of emulsifier of the formula I, where R ¹ in compounds of the formula I can also be a C ₆ -C ₃₀ -alkyl or -alkenyl group;
• b) 2 to 20 wt .-% of an oil phase, not with water miscible organic liquid;
• c) 2 to 30 wt .-% water and / or at least one with water miscible organic liquid;
• d) 40 to 90% by weight of an inorganic oxidizing agent;
• e) 0 to 25 wt .-% of usual other explosives, such as Density-adjusting agents, flammable inorganic or orga African solids.

The invention also relates to a method for the production such liquid explosive compositions, wherein the or the emulsifiers in an organic liquid forming the oil phase dissolves, the organic solution is optionally heated and an optionally heated aqueous phase is emulsified therein, wel surface comprises an inorganic oxidizing agent.

Another object of the invention relates to fuel together Settings containing a major amount of a hydrocarbon a fuel protecting against wear and / or corrosion  sion inhibiting amount and / or acting as a detergent additive at least one compound of the general formula I.

Another object of the invention relates to lubricants together solutions containing a major amount of a liquid, semi-solid or solid lubricant an effective amount little least one compound of general formula I.

The invention also relates to fuel additive packages holding at least one ver in addition to conventional fuel additives binding of formula I.

The invention further relates to the use of a compound of the formula I as defined above, as an emulsifier for liquid explosives, where R ¹ in compounds of the formula I can also represent a C ₆ -C ₃₀ alkyl or alkenyl group; and the use of a compound of formula I as defined for water-in-fuel emulsions or as a wear protection additive, corrosion protection additive or detergent additive in hydrocarbon fuels and / or lubricants.

A final object of the invention relates to a process for the preparation of a compound of formula I, which is characterized in that an amine of formula II

R ¹ R ² NH (II)

wherein R ¹ and R ^{2 have} the meanings given above, with a compound of the formula (III)

X (C = O) R ⁴ (III)

wherein (C = O) R ^{4 has} the meanings given for R ³ , and X stands for OH, halogen, OC ₁ -C ₆ alkyl, or O (C = O) R ^4a , where (C = O) R ^4a has the meanings given for R ³ or represents the remainder of a mono- or polycarboxylic acid which does not carry any hydroxy or amino groups.

Compounds of the general formula I

In the compounds of the general formula I, R ¹ preferably represents straight-chain or branched alkyl, alkenyl, alkyl aryl or alkenyl aryl radicals. Preferred alkyl or alkenyl groups have a number average molecular weight M _N of 200 or more, in particular about 400 or 500 and more, such as. B. 1000 or more. The M _N upper limit is about 10,000, preferably about 5000. The alkenyl group can contain one or more, such as, for. B. 1 to 20, preferably isolated, double bonds. R ¹ can optionally carry additional polar substituents, in particular one or more OH or NH ₂ groups, preferably close to the nitrogen atom to which R ^{1 is} bonded.

The aryl group of R ¹ is preferably derived from mononuclear or dinuclear condensed or uncondensed 4- to 7-membered, in particular 6-membered aromatic or heteroaromatic groups such as phenyl, pyridyl, naphthyl and biphenyl. The alkyl or alkenyl groups bonded to the aryl group can also have a chain length of 1 or 2 to 30 carbon atoms or more, such as, for. B. from 31 to 400 carbon atoms, and also be straight-chain or branched.

R ² in compounds of the formula I can in particular stand for:

• a) H;
• b) a C ₁ -C ₁₈ alkyl radical; Examples of suitable alkyl radicals are straight-chain or branched radicals having 1 to 18 carbon atoms, such as methyl, ethyl, i- or n-propyl, n-, i-, sec- or tert-butyl, n- or i-pentyl; also n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-tridecyl, n-tetradecyl, n-pentadecyl and n-hexadecyl and n-octadecyl and the one or more times branched analogues thereof; and corresponding radicals in which the carbon chain has one or more ether bridges;
• c) a C ₂ -C ₁₈ alkenyl radical; examples of suitable alkenyl radicals are the mono- or polysaturated, preferably mono- or di-unsaturated analogues of the above-mentioned alkyl radicals having 2 to 18 carbon atoms, it being possible for the double bond to be in any position in the carbon chain;
• d) a C ₄ -C ₁₈ cycloalkyl radical; Examples include cyclobutyl, cyclopentyl and cyclohexyl, and the analogues thereof substituted with 1 to 3 C ₁ -C ₄ alkyl radicals; wherein the C ₁ -C ₄ alkyl z. B. are selected from methyl, ethyl, i- or n-propyl, n-, i-, sec- or tert-butyl;
• e) a C ₁ -C ₁₈ alkyl aryl radical or a C ₂ -C ₁₈ alkenyl aryl radical; wherein the C ₁ -C ₁₈ alkyl or C ₂ -C ₁₈ alkenyl group is as defined above and the aryl group has the same meanings as the aryl group of R ¹ defined above;
• f) a hydroxy-C ₁ -C ₁₈ alkyl radical; this one or more times, preferably simply, such as. B. simply terminally hydroxylated analogs of the above C ₁ -C ₁₈ alkyl radicals; Examples include 2-hydroxy-ethyl, 2-hydroxy- and 3-hydroxypropyl;
• g) an optionally hydroxylated poly (oxyalkyl) radical, which can be obtained by alkoxylation of the N atom with 2 to 10 C ₂ -C ₁₀ alkoxy groups, where individual carbon atoms can optionally carry further hydroxyl groups. Preferred alkoxy groups include ethoxy and n- and iso-propoxy groups;
• h) a polyalkylene polyamine radical of the formula
  Z-NH- (C ₁ -C ₆ alkylene-NH) _m -C ₁ -C ₆ alkylene,
  wherein m is an integer from 0 to 5, Z is H or C ₁ -C ₆ alkyl and C ₁ -C ₆ alkyl is a radical such as methyl, ethyl, i- or n-propyl, n-, i- , sec.- or tert.-butyl, n- or i-pentyl; also stands for n-hexyl; and C ₁ -C ₆ alkylene represents the corresponding bridged analogs of these radicals;
• i) a polyalkyleneimine radical composed of 1 to 10 C ₁ -C ₄ -alkyleneimine groups, in particular ethyleneimine groups;
• j) R ¹ and R ² may also or together with the nitrogen atom to which they are attached, represent an optionally substituted 5- to 7-membered heterocyclic ring, optionally substituted with one to three alkyl radicals, which optionally has a further ring heteroatom, such as O or N, and has a total of about 6 to 400 carbon atoms.

In particularly preferred compounds of formula I R ^{1 is} derived from polyisobutenes. Particularly suitable polyisobutenes are so-called "highly reactive" polyisobutenes, which are distinguished by a high content of terminally arranged ethylenic double bonds. Suitable highly reactive polyisobutenes are, for example, polyisobutenes which have a proportion of vinylidene double bonds of more than 70 mol%, in particular more than 80 mol% and in particular more than 85 mol%. Polyisobutenes which have uniform polymer skeletons are particularly preferred. A uniform polymer structure has in particular those polyisobutenes which are composed of at least 85% by weight, preferably at least 90% by weight and particularly preferably at least 95% by weight, of isobutene units. Such highly reactive polyisobutenes preferably have a number average molecular weight M _N in the range mentioned above. In addition, the highly reactive polyisobutenes can have a polydispersity of less than 1.9, such as. B. less than 1.5. Polydispersity is the quotient of the weight-average molecular weight M _{W divided} by the number-average molecular weight M _N.

Particularly suitable highly reactive polyisobutenes are e.g. B. the Glissopal® brands from BASF AG, in particular Glissopal 1000 (M _N = 1000), Glissopal V 33 (M _N = 550) and Glissopal 2300 (M _N = 2300) and their mixtures. Other number average molecular weights can be adjusted in a manner known in principle by mixing polyisobutenes of different number average molecular weights or by extractive enrichment of polyisobutenes of certain molecular weight ranges.

R ³ in compounds of the formula I is an acyl radical of a mono- or polycarboxylic acid and carries at least one free hydroxy or primary, secondary of the tertiary amino group. In particular, R ³ stands for (C = O) R ⁴ , where R ⁴ can stand for:

• a) hydroxy or amino-C ₁ -C ₁₈ alkyl; wherein the hydroxy or amino group is attached in any chain position and the alkyl group is as defined above;
• b) hydroxy or amino-C ₂ -C ₁₈ alkenyl; wherein the hydroxy or amino group is attached in any chain position and the alkenyl group is as defined above;
• c) hydroxy or amino-C ₄ -C ₁₈ cycloalkyl; wherein the hydroxy or amino group is bound in any position and the cycloalkyl group is as defined above;
• d) hydroxy or amino-C ₁ -C ₁₈ alkyl aryl; wherein the hydroxy or amino group is bound in any position and the alkyl aryl group is as defined above;
• e) hydroxy or amino-C ₂ -C ₁₈ alkenyl aryl radicals; the hydroxy or amino group being bound in any position and the alkyl aryl group being as defined above;
• f) residues of groups a) to e), which additionally at least a further, in particular one or two further carboxyls carry groups;
• g) Amino-substituted radicals of groups a) to f), where amino group carries one or two identical or different hydroxy-C ₁ -C ₄ alkyl groups.

The acyl radicals R ³ are derived from generally available or conventionally producible carboxylic acids or carboxylic acid derivatives, such as halides, esters, or anhydrides.

Preparation of compounds of formula I:
The compounds of formula I are carboxamides and as such are easily accessible by reacting a suitable primary or secondary amine of formula II above with a suitable carboxylic acid or a suitable carboxylic acid derivative of the above formula III.

The carboxylic acids or carboxylic acid derivatives which can be used according to the invention are compounds which are known per se or are accessible in a known manner. Preferred examples of particularly suitable carboxylic acids of the formula III include:

• a) monohydroxy-monocarboxylic acids, such as hydroxyacetic acid, alpha- Hydroxypropionic acid, alpha-hydroxybutyric acid, alpha-hydroxy valeric acid, mandelic acid and the positional isomers of these Links;
• b) monohydroxy-dicarboxylic acids, such as. B. tartronic acid, malic acid, hydroxyglutaric;
• c) monohydroxy polycarboxylic acids, such as citric acid;
• d) polyhydroxy monocarboxylic acids, such as glyceric acid and glucon acid;
• e) polyhydroxy-polycarboxylic acids, such as tartaric acid; and
• f) amino acids, such as serine, threonine, aspartic acid, glutamine acid and lysine.

The amines of the formula II which can be used according to the invention are compounds which are known or can be prepared in a known manner. In particular, the amines used are primary or secondary monoamines or polyamines with a pronounced hydrophobic hydrocarbyl radical R ¹ as defined above.

Hydrocarbylamines of this type and their preparation are in described for example in: EP-A-0 244 616, EP-A-0 578 323, WO-A-94/24231, DE-A-196 20 262, DE-A-43 13 088, whereupon hereby explicit reference is made.  

Preferred examples of particularly suitable amines of the formula II include polyalkenamines and especially polyisobutene amines. This are particularly preferred by hydroformylation and subsequent ßende reductive amination of a suitable polyalkene (EP-A 0 244 616), by amination of a polyalkenepoxide and on closing catalytic dehydration and hydrogenation (DE-A-196 20 262), by alkylation of an amine with an alkyl halide (DE-A-21 29 461 or DE-A-22 45 918) accessible. except corresponding connections can be made through implementation an amine with phosphosulfurized polyalkylene (cf. DE-A-12 85 658). Particularly preferred amines are among the Han The Kerocom PIBA name is available from BASF AG.

Suitable reaction conditions for the preparation of compounds genes of formula I are known to those skilled in the art or less Preliminary tests can be determined. The direct order is particularly preferred settlement of the carboxylic acid with the amine to the acid amide under the same early removal of the water of reaction formed.

Amide formation is preferred at a temperature of about 20 ° C up to 250 ° C. Tem are particularly suitable for reaction temperatures in the range of 100 to 200 ° C. To remove the reacti onswassers can preferably under reduced pressure, for. B. in Range from about 5 to 50 mbar.

The amide formation is preferably carried out in a liquid medium carried out. For this purpose, the reactants in a suitable or ganic solvent, optionally with heating, dissolved. Suitable solvents for carrying out this reaction are especially high-boiling (boiling points in the range of about 180 up to 350 ° C) hydrocarbons or mixtures of such hydrocarbons fabrics such as B. mineral oils.

The reaction time is about 10 minutes to 20 hours. To when the reaction has ended, the mixture is filtered, if appropriate, preferably hot and further cleaned.

Water-in-fuel emulsions

The emulsifiers of the formula I according to the invention are suitable for for example for the production of stable water-in-oil emulsions, such as in particular water-in-fuel emulsions, wherein in one Bulk of a common hydrocarbon fuel water in up to about 35% by weight, e.g. B. about 0.2 to 10 or 0.5 to 5% by weight is emulsified.  

In such emulsions according to the invention, the emulsified water can contain a certain amount of one or more C ₁ -C ₄ alcohols. The amount of alcohol used is from 5 to 50% by weight, based on the amount of water. The temperature range in which the emulsion is stable can be broadened by adding alcohol.

In addition to the components mentioned above, the emulsions according to the invention can include fuel, water, amide emulsifier and, if appropriate, C ₁ -C ₄ alcohol, and other customary components. On the one hand, these are other surfactants that also serve as emulsifiers. For this purpose, for example, are sodium lauryl sulfate, quaternary ammonium salts, alkyl glycosides, lecithins, polyethylene glycol ethers, sorbitan oleates, stearates and polyethylene -laurate and lenglykolester, sorbitan monooleate or sorbitan nooleatethoxylat preferably, C ₈ -C ₁₈ alcohol ethoxylates and late Alkylphenolethoxy, for example octyl and nonylphenol ethoxylates and Ricinu oil ethoxylates. If these further surfactants are used, this occurs in amounts of 0.5 to 5% by weight, preferably 1 to 2.5% by weight, based on the overall composition.

Within the scope of the present invention, fuel-what Produce water emulsions from all common types of fuel. Examples of preferred fuels are diesel fuel, Otto fuel, kerosene, heavy and light heating oil.

For the production of particularly preferred water according to the invention The emulsifier according to the invention becomes in-fuel microemulsions optional with the fuel, the water and the others Deten components and emulsified in a conventional manner. at for example, the emulsification in a rotor mixer, per Mixing nozzle or ultrasonic probe. Preferably poses emulsions with an average droplet size of the emul gated phase of about 0.5 to 5 microns, preferably <2 microns ago.

explosive compositions

The emulsifiers of the formula I according to the invention are white furthermore for the preparation of explosive compositions. such Compositions according to the invention contain in solid, pasty or preferably liquid state an oil-in-water or before preferably a water-in-oil emulsion, produced using at least one of the emulsifiers described above.

In the explosive compositions according to the invention, the oil is phase-forming, water-immiscible organic liquid in a proportion of about 2 to 20% by weight, preferably about 2 to  12 wt .-%, in particular about 3 to 8 wt .-%, based on the Ge total weight of the composition included. The actually turned on set amount varies depending on the each used organic liquids. The organic liquid can be aliphatic, alicyclic, and / or aromatic and ge have saturated or unsaturated character. Is preferred the organic liquid used in the manufacture of the Liquid formulation. Preferred liquids include tall oil, mineral oils, waxes, paraffin oils, benzene, toluene, xylene, mi deposits of liquid hydrocarbons, which also under the Sam mel Oil crude distillates are known, such as. B. Gasolin, Kero sin and diesel fuel, as well as vegetable oils, such as corn oil, Cottonseed oil, peanut oil and soybean oil. Particularly preferred organic liquids are mineral oil, paraffin waxes, micro crystalline waxes and mixtures thereof. Aliphatic and aromatic nitrogen compounds are also applicable.

In the compositions according to the invention in a proportion up to 15% by weight, e.g. B. about 1 to 12 wt .-%, more ex Liche solid or liquid flammable or oxidizable, inorganic or organic substances or mixtures thereof. Examples include: aluminum particles, magnesium particles, carbonaceous materials such as B. carbon black, vegetable granu lat, such as B. wheat granules, and sulfur.

As an inorganic oxidizing agent, which is part of the dis is continuous, aqueous phase, contain the Invention compositions in a proportion of about 40 to 95 wt .-%, such as. B. about 50 to 90 wt .-%, based on the Ge total weight of the composition at least one inorganic Salt dissolved in water and / or a water-miscible orga African liquid, which is in a proportion of about 2 to about 30 wt .-%, based on the total weight of the composition ent hold is. Suitable salts are alkali, alkaline earth or ammonium umnitrate, chlorate or perchlorate. Examples of suitable ones Oxidizing agents are sodium nitrate, sodium chlorate, sodium perchlorate, potassium nitrate, calcium chlorate, calcium perchlorate, Ka lium nitrate, potassium chlorate, potassium perchlorate, ammonium chlorate, Am monium perchlorate, lithium nitrate, lithium chlorate, lithium perchlo Rat, magnesium nitrate, magnesium chlorate, magnesium perchlorate, aluminum minium nitrate, aluminum chlorate, barium nitrate, barium chlorate, Ba rium perchlorate, zinc nitrate, zinc chlorate, zinc perchlorate, ethylene diamine dichlorate and ethylenediamine diperchlorate. preferred Oxidizing agent is ammonium, sodium and / or calcium nitrate. About 10 to 65 wt .-% of the total oxidizing agent can kri may be contained in stallin or particulate form.  

Water is generally present in a proportion of about 2 to 30 wt .-%, based on the total weight of the composition set. Water can also be combined with one with water miscible organic liquid used to be given if necessary to improve the solubility of the salts used or to change the crystallization temperature of the salts. With Water-miscible organic liquids are, for example, Al alcohols, such as methyl alcohol, glycols, such as ethylene glycol, amides, such as Formamides and analogous nitrogenous liquids.

Used as an emulsifier for the dispersion of the aqueous phase preferably about 1 to 20% by weight of a compound of the formula I or a mixture of such compounds. If necessary, NEN customary emulsifying additives are used. As Non-limiting examples can be found in the above Compounds described in the prior art, in particular the mentioned PIBSA derivatives or sorbitan fatty acid esters become. In small amounts, such as B. 0.1 to 5 wt .-% based on the total weight of the composition, other übli can che, known from the prior art emulsifiers such. B. be wrote in Ullmann's Encyclopedia of Industrial Chemistry, 5. Edition, volume A9, pp. 313-318, can be used.

Means for adjusting the Density of the composition can be used. The density of he Compositions according to the invention are in the range of about 0.5 to about 1.5 g / ccm. Suitable means for density adjustment are for example glass beads, plastic beads, pearlite or foam-forming or gas-forming agents.

The explosive compositions according to the invention are in her formulated conventionally. Usually this is solved first Oxidizing agent in water or an aqueous solution at a Temperature in the range of, for example, about 20 to 90 ° C. The aqueous solution then becomes a solution of the emulsifier and water-immiscible organic liquid. The organic solution is also at a similarly high tem temperature heated like the aqueous solution. The resulting Ge is mixed to produce a uniform water-in-oil emul sion stirred. Other solid components that may be present then stirred into the emulsion.

Fuel and lubricant compositions

The present invention also relates to fuel compositions, especially diesel and petrol together settlements, which the amides according to the invention in effective amounts  contain. Taking effective amounts are usually at strength substance compositions 10 to 5000 ppm and in particular 20 to 2000 ppm, based on the total amount of fuel composition tongue to understand.

The present invention also relates to lubrication substance compositions, especially lubricant compositions conditions, the 0.1 to 10 wt .-%, in particular 0.5 to 5 wt .-%, bezo to the total amount of lubricant composition that he contain amides according to the invention.

The present invention furthermore relates to additive cones concentrates, especially fuel additive concentrates and lubricants substance additive concentrates, particularly preferably fuel additive Concentrates containing little in addition to conventional additive components least an amide according to the invention in proportions of 0.1 to 80 wt .-%, in particular 0.5 to 60 wt .-%, based on the Ge total weight of the concentrate.

As a solvent or diluent (if Addi tive packages) come aliphatic and aromatic hydrocarbons fabrics, e.g. B. Solvent Naptha.

When used as a fuel or lubricant additive, the amides according to the invention can advantageously be combined with other conventional detergent additives. Suitable additives with detergent action are, for example, those which have at least one hydrophobic hydrocarbon radical with a number-average molecular weight (M _N ) of 85 to 20,000 and at least one polar grouping selected from

• a) mono- or polyamino groups with up to 6 nitrogen atoms, where at least one nitrogen atom has basic properties Has,
• b) nitro groups, possibly in combination with hydroxyl groups,
• c) hydroxyl groups in combination with mono- or polyamino groups pen, where at least one nitrogen atom is a basic property has,
• d) carboxyl groups or their alkali metal or alkaline earths tallsalzen,
• e) sulfonic acid groups or their alkali metal or alkaline earths tallsalzen,  
• f) polyoxy-C ₂ -C ₄ -alkylene groups which are terminated by hydroxyl groups, mono- or polyamine groups, where at least one nitrogen atom has basic properties, or by carbamate groups,
• g) Carbonsäureestergruppen,
• h) groups derived from succinic anhydride with Hy droxy and / or amino and / or amido and / or imido groups and
• i) by Mannich reaction with phenolic hydroxyl groups Aldehydes and mono- or polyamines generated groups

exhibit.

The hydrophobic hydrocarbon residue in these detergent additives, which ensures sufficient solubility in the fuel, has a number average molecular weight (M _N ) from 85 to 20,000, in particular from 113 to 10,000, especially from 300 to 5,000. As a typical hydrophobic hydrocarbon residue, especially in Compound with the polar groups (a), (c), (h) and (i), the polypropenyl, polybutenyl and polyisobutenyl radicals come with in each case M _N = 300 to 5000, in particular 500 to 2500, especially 750 to 2250.

Examples of further fuel additives with polar groupings (a) are polyalkene mono- or polyalkene polyamines or functional derivatives thereof based on polypropene, polybutene or polyisobutene. Examples of polyalkenamines are poly-C ₂ -C ₆ -alkenes or functional derivatives thereof. These compounds can have a number average molecular weight M _N of 300 to 5000. Particularly preferred detergent additives are selected from polyisobutenamines and functional derivatives thereof, as described for example in EP-A-0 244 616 and EP-A-0 578 323. The polyisobutenamines usually have a number average molecular weight M _N in the range from about 150 to about 5000, preferably about 500 to 2000, in particular about 800 to 1500 g, per mole.

Examples of other fuel additives with polar groupings gene (b) are the reaction products of polyisobutenes with a average degree of polymerization P = 5 to 100 with nitrogen oxides or Mixtures of nitrogen oxides and oxygen.  

Examples of further fuel additives with polar groups (c) are the reaction products of polyisobutene epoxides, which are obtainable from polyisobutene having predominantly terminal double bonds and having a number-average molecular weight M _N in the range from 300 to 5000, with ammonia, mono- or polyamines.

Examples of further fuel additives with polar groupings (d) are copolymers of C ₂ -C ₄₀ -olefins with maleic anhydride with a total molecular weight of 500 to 20,000, the carboxyl groups of which, in whole or in part, form the metal salts to the alkali metal or alkaline earth metals and a remaining one The rest of the carboxyl groups are reacted with alcohols or amines.

Examples of other fuel additives with polar groupings gene (e) are alkali metal or alkaline earth metal salts of a sul fobernsteinsäurealkylesters.

Examples of further fuel additives with polar groupings (f) are polyethers or polyetheramines or functional derivatives thereof, which can be obtained by reacting C ₂ -C ₃₀ -alkanols, C ₆ -C ₆₀ -alkaniols, mono- or di-C ₂ - C ₃₀ alkyl amines, C ₁ -C ₃₀ alkylcyclohexanols or C ₁ -C ₃₀ alkyl phenols with 1 to 30 mol ethylene oxide and / or propylene oxide and / or butylene oxide per hydroxyl group or amino group and, in the case of the polyether amines, by subsequent reductive Amination with ammonia, monoamines or polyamines are available. For example, poly-C ₂ -C ₆ alkylene oxide amines or functional derivatives thereof can be used as polyether amines.

Examples of other fuel additives with polar groupings gene (g) are esters of mono-, di- or tricarboxylic acids with long chain alkanols or polyols.

Examples of further fuel additives with polar groupings (h) are derivatives of polyisobutenyl succinic anhydride, which are obtainable by reaction of conventional or highly reactive poly isobutene with M _N = 300 to 5000 with maleic anhydride by thermal means or via the chlorinated polyisobutene.

Examples of other fuel additives with polar groupings gene (i) are the reaction products of polyisobutene-substituted phenols with formaldehyde and mono- or polyamines.

Further fuel additives with detergent effects are further the following examples are given as examples.  

Additives containing mono- or polyamino groups (a) are preferably polyalkene mono- or polyalkene-polyamines based on polypropene or highly reactive (ie with mostly terminal double bonds mostly in the β- and γ-position) or conventional (ie with predominantly central double bonds) ) Polybutene or polyisobutene with M _N = 300 to 5000. Such additives based on highly reactive polyisobutene, which from the polyisobutene, which can contain up to 20 wt .-% n-butene units, by hydroformylation and reductive amination with ammonia, monoamines or polyamines, such as dimethylaminopropylamine, ethylenediamine, diethylenetriamine, triethylenetetramine or tetraethylene pentamine, can be prepared, are known in particular from EP-A-0 244 616. If one starts with the production of additives from polybutene or polyisobutene with mostly double bonds in the middle (mostly in the beta and gamma position), the production route by chlorination and subsequent amination or by oxidation of the double bond with air or ozone is available Carbonyl or carboxyl compound and subsequent amination under reductive (hydrogenating) conditions. For amination, the same amines as above for the reductive amination of the hydroformylated, highly reactive polyisobutene can be used. Corresponding additives based on polypro pen are described in particular in WO-A-94/24231.

Other preferred additives containing monoamino groups (a) are the hydrogenation products of the reaction products from polyisobutenes with an average degree of polymerization P = 5 to 100 with Sticko xides or mixtures of nitrogen oxides and oxygen, as they ins are particularly described in WO-A-97/03946.

Other preferred additives containing monoamino groups (a) are the polyisobutene epoxides by reaction with amines and after following dehydration and reduction of the amino alcohols union compounds, as described in particular in DE-A-196 20 262 are described.

Nitro groups, optionally in combination with hydroxyl groups, (b) ent holding additives are preferably reaction products made of poly isobutenes of average degree of polymerization P = 5 to 100 or 10 to 100 with nitrogen oxides or mixtures of nitrogen oxides and Oxygen, as described in particular in WO-A-96/03367 and in WO A 96/03479 are described. These implementation products provide usually mixtures of pure nitropolyisobutanes (e.g. al pha, beta-dinitropolyisobutane) and mixed hydroxynitropolyiso butanes (e.g. alpha-nitro-beta-hydroxypolyisobutane).  

Additives containing hydroxyl groups in combination with mono- or polyamino groups (c) are, in particular, reaction products of polyisobutene epoxides, obtainable from polyisobutene preferably having predominantly double bonds with M _N = 300 to 5000, with ammonia, mono- or polyamines, as described in particular in the EP -A-476 485.

Additives containing carboxyl groups or their alkali metal or alkaline earth metal salts (d) are preferably copolymers of C ₂ -C ₄₀ olefins with maleic anhydride with a total molar mass of 500 to 20,000, the carboxyl groups of which are wholly or partly associated with the alkali metal or alkaline earth metal salts and remain The rest of the carboxyl groups are reacted with alcohols or amines. Such additives are known in particular from EP-A-307 815. Such additives are mainly used to prevent valve seat wear and, as described in WO-A-87/01126, can advantageously be used in combination with conventional fuel detergents such as poly (iso) butenamines or polyetheramines.

Sulphonic acid groups or their alkali metal or alkaline earth metal additives containing salts (s) are preferably alkali metal or alkaline earth metal salts of an alkyl sulfosuccinic acid ester, as described in particular in EP-A-639 632. Derar additives are mainly used to prevent valves seat wear and can be used in combination with usual Fuel detergents such as poly (iso) butenamines or polyethera mines are used.

Additives containing polyoxy-C ₂ -C ₄ -alkylene groups (f) are preferably polyethers or polyetheramines which are obtained by reacting C ₂ -C ₆₀ -alkanols, C ₆ -C ₃₀ -alkanediols, mono- or di-C ₂ - C ₃₀ alkylamines, C ₁ -C ₃₀ alkylcyclohexanols or C ₁ -C ₃₀ alkylphenols with 1 to 30 mol ethylene oxide and / or propylene oxide and / or butylene oxide per hydroxyl group or amino group and, in the case of the polyetheramines, by subsequent reductive amination with Am moniak, monoamines or polyamines are available. Such products are described in particular in EP-A-310 875, EP-A-356 725, EP-A-700 985 and US-A-4 877 416. In the case of polyethers, such products also have carrier oil properties. Typical examples are tridecanol or isotridecanol butoxylates, isononylphenol butoxylates and polyisobutenol butoxylates and propoxylates as well as the corresponding reaction products with ammonia.

Additives containing carboxylic acid ester groups (g) are preferably esters of mono-, di- or tricarboxylic acids with long-chain alkanols or polyols, in particular those with a minimum viscosity of 2 mm ² / s at 100 ° C., as described in particular in DE-A- 38 38 918 are described. Aliphatic or aromatic acids can be used as mono-, di- or tricarboxylic acids; long-chain representatives with, for example, 6 to 24 carbon atoms are particularly suitable as ester alcohols or polyols. Typical representatives of the esters are adipates, phthalates, isophthalates, terephthalates and trimellitates of isooctanol, isononanol, iso decanol and isotridecanol. Such products also have carrier oil properties.

Groups derived from succinic anhydride and containing hydroxyl and / or amino and / or amido and / or imido groups (h) are preferably corresponding derivatives of polyisobutenylsuccinic anhydride which are obtained by reacting conventional or highly reactive polyisobutene with M _N = 300 to 5000 with maleic anhydride are available thermally or via the chlorinated polyisobutene. Of particular interest are derivatives with aliphatic polyamines such as ethylene diamine, diethylene triamine, triethylene tetramine or tetraethylene pentamine. Such gasoline fuel additives are described in particular in US-A-4,849,572.

Groups (i) containing additives produced by Mannich reaction of phenolic hydroxyl groups with aldehydes and mono- or polyamines are preferably reaction products of polyisobutene-substituted phenols with formaldehyde and mono- or polyamines such as ethylenediamine, diethylenetriamine, triethylenetetra min. Tetraethylene pentamine or dimethylaminopropylamine. The poly isobutene-substituted phenols can come from conventional or highly reactive polyisobutene with M _N = 300 to 5000. Such "polyisobutene Mannich bases" are described in particular in EP-A-831 141.

Further detergent additives which are suitable according to the invention are described, for example, in European patent applications EP-A-0 277 345, 0 356 725, 0 476 485, 0 484 736, 0 539 821, 0 543 225, 0 548 617, 0 561 214, 0 567 810 and 0 568 873; in German patent applications DE-A-39 42 860, 43 09 074, 43 09 271, 43 13 088, 44 12 489, 0 44 25 834, 195 25 938, 196 06 845, 196 06 846, 196 15 404, 196 06 844, 196 16 569, 196 18 270 and 196 14 349; as well as in WO-A-96/03479. Particularly useful detergent additives are sold by BASF AG, Ludwigshaven, under the trade name Kerocom PIBA. These contain polyisobutenamines dissolved in aliphatic C ₁₀ -C ₁₄ hydrocarbons. The detergent additives used according to the invention, in particular the polyisobutenamine additives used with preference, usually have a number-average molecular weight M _N in the range from about 150 to about 5000, preferably about 500 to 2000, in particular about 800 to 1500 g, per mole.

For a more precise definition of the individual fuel wheel listed ditive here on the revelations of the above-mentioned document State of the art expressly referred.

The fuel additives used according to the invention or thus ad ditivated fuels can in addition to the carrier oils and Detergent additives and other common components and additives contain such. B. further carrier oils, corrosion inhibitors, De emulsifiers and dyes.

Carrier oils can also be mentioned as further customary components. Here are, for example, mineral carrier oils (base oils), especially those of the viscosity class "Solvent Neutral (SN) 500 to 2000", synthetic carrier oils based on olefin polymers with M _N = 400 to 1800, especially based on polybutene or polyisobutene ( hydrogenated or not hydrogenated), of polyalphaolefins or polyinternalolefins and synthetic carrier oils based on alkoxylated long-chain alcohols or phenols. Also suitable as further additives are polyalkylene alcohol-polyetheramines, as described, for example, in DE-199 16 512.2.

Examples of suitable synthetic carrier oils are polyolefins, (Poly) esters, and polyethers, aliphatic polyether amines, alkyl phenol started polyethers and alkylphenol started polyethers Ramine. Suitable carrier oil systems are described, for example in DE-A-38 38 918, DE-A-38 26 608, DE-A-41 42 241, DE-A-43 09 074, US 4,877,416 and EP-A-0 452 328, which hereby refers to is expressly referred to.

Other common additives are corrosion inhibitors, for example wise based on ammonium salts or film ganic carboxylic acids or heterocyclic aromatics Non-ferrous metal corrosion protection, antioxidants or stabilizers, for example based on amines such as p-phenylenediamine, dicy clohexylamine or derivatives thereof or of phenols such as 2,4-di tert-butylphenol or 3,5-di-tert-butyl-4-hydroxyphenylpro pionic acid, demulsifiers, antistatic agents, metallocenes such as ferro cen or methylcyclopentadienylmanganese tricarbonyl, lubricious improvement agents (lubricity additives) such as certain fatty acids, Alkenyl succinic acid esters, bis (hydroxyalkyl) fatty amines, hydroxya  cetamide or castor oil and dyes (markers). It can too Amines added to lower the pH of the fuel.

The compounds of the formula I according to the invention develop theirs anticorrosive effect not only when used as a strength or Lubricant additive. Anti-corrosive properties are also at their use in aqueous systems, such as. B. Radiator fluid or drilling and cutting fluids observed. such anti-corrosive liquids are also the subject of the invention dung. These can be the compounds of the invention in one Proportion of about 1 to 10% by weight, optionally in combination with contain other common anti-corrosive additives.

The present invention will now be described with reference to the fol ing non-limiting exemplary embodiments explained in more detail.

example 1 Production of the emulsifiers a) Preparation of the emulsifier A

Polyisobutylenamine (185 g, Mw = 1000, 55% by weight in mineral oil, Kero com®PIBA from BASF AG) was mixed with gluconic acid (24.3 g, 50% by weight in Water, ADM oil mills) and heated at 170 W for 2 hours. After no more water had distilled off, the product was removed cools and bottled.

b) Preparation of the emulsifier B

Polyisobutylenamine (185 g, Mw = 1000, 55% by weight in mineral oil, Kero com®PIBA from BASF AG) was mixed with glyceric acid (15.7 g, 40% in Water, TCI, Tokyo Kasei) and 2 hours at 170 ° C hitzt. After no more water was distilled off, the product cooled and bottled.

c) Preparation of the emulsifier C

Polyisobutylene amine (73 g, Mw = 1000, 55% by weight in mineral oil, Kero com®PIBA from BASF AG) was mixed with lactic acid (4 g, Merck, Darm city, 90% by weight in water) and 2 hours at 170 ° C hitzt. After no more water was distilled off, the product cooled and bottled.

d) Preparation of the emulsifier D

Tallow fatty amine (54 g, Radiamin 6171 from Fina Chemicals, Brüs sel) was dissolved in mineral oil (54 g), with gluconic acid (82 g, 50% in water, ADM oil mills) and heated at 170 ° C. for 2 hours. After no more water had distilled off, the product was removed cools and bottled.  

e) Production of emulsifiers E and F

500 g polyisobutylene amine (Mw = 1000, 55% by weight in mineral oil, Kero com®PIBA from BASF AG) was treated with 65 g L-glutamic acid (E) or 60 g of L-aspartic acid (F) and at 160 ° C under vacuum hitzt. After no more water was distilled off, the product filtered hot, cooled and bottled.

Example 2 Preparation of a liquid explosive emulsion a) Preparation of emulsion A

30 parts of emulsifier A were dissolved in 50 parts of mineral oil and heated to 70 ° C. This solution was stirred vigorously 1100 parts of heated ammonium nitrate solution (80% by weight in water, 80 ° C) added. The emulsion thus obtained was at room temperature door cooled, it was transparent and showed even after 2 months ger storage no separation or crystallization tendency. A Sample was overlaid with water and also showed several No breakup of the emulsion for several weeks.

b) Preparation of emulsion B

30 parts of emulsifier B were dissolved in 50 parts of mineral oil and heated to 70 ° C. This solution was stirred vigorously 1100 parts of heated ammonium nitrate solution (80% by weight in water, 80 ° C) added. The emulsion thus obtained was at room temperature door cooled, it was transparent and showed even after 2 months ger storage no separation or crystallization tendency. A Sample was overlaid with water and also showed several No breakup of the emulsion for several weeks.

c) Preparation of the emulsion C

30 parts of emulsifier C were dissolved in 50 parts of mineral oil and heated to 70 ° C. This solution was stirred vigorously 1100 parts of heated ammonium nitrate solution (80% by weight in water, 80 ° C) added. The emulsion thus obtained was transparent at 70 ° C rent, but showed weak separation and cooling after cooling Crystallization.

d) Preparation of the emulsion D

30 parts of emulsifier D were dissolved in 50 parts of mineral oil and heated to 70 ° C. This solution was stirred vigorously 1100 parts of heated ammonium nitrate solution (80% by weight in water, 80 ° C) added. The emulsion thus obtained was at room temperature door cooled, it was transparent and showed even after 2 months ger storage no separation or crystallization tendency. A Sample was covered with water and already showed after meh After a few days the emulsion breaks open.  

e) Comparative example

15 parts of sorbitan monooleate (S-MAZ 80 from BASF Corp.) were in 55 parts of mineral oil dissolved and heated to 70 ° C. In this solution 1100 parts of heated ammonium nitrate were dissolved with vigorous stirring Solution (80 wt .-% in water, 80 ° C) added. The emul thus obtained sion was cooled to room temperature, it was transparent and showed no separation or crises even after 2 months of storage stallisationsneigung. A sample was overlaid with water and showed a breakup of the emul after several days sion.

Example 3 Preparation of a water-fuel emulsion

a) A 2% solution of an emulsifier mixture was prepared, consisting of 6 parts from emulsifiers A and E, 3 parts from a C ₁₃ oxo alcohol ethoxylate (7 EO) (Lutensol TO 7 from BASF AG) and composed of 2 parts from an alkylphenol ethoxylate (Emulan OP 25). With an Ultra-Turrax (Jahnke and Kun kel laboratory device T 25) 500 g of this mixture were mixed with 100 ml of water (15 minutes at 24000 rpm). The emulsion obtained in this way showed no signs of phase separation after 4 weeks of storage.

b) For a comparative example instead of the invention Emulsifiers 6 parts of sorbitan monooleate (S-MAZ 80 from BASF Corp.) used. After 3 weeks, the bottom of the glass container the first drop formation (phase separation) was observed.

Example 4 Determination of wear protection behavior in force materials

It was in an unadditized diesel fuel (Miro-Karls rest) solved the substances listed in Table 1. There have been Weil made mixtures with 75 ppm additive. The assessment was carried out by HFRR test (High Frequency Roller Rig Test), which according to ISO 12156-1 was carried out. The length of the resulting striae is measured and used as a measure of wear.  

Table 1

Results of the HFRR measurement

Claims (17)

1. Compound of the general formula I
R ¹ R ² NR ³ (I)
wherein
R ^{1 represents} a C ₃₁ -C ₄₀₀ alkyl or C ₃₁ -C ₄₀₀ alkenyl group, C ₈ -C ₄₀₀ alkyl aryl or a C ₈ -C ₄₀₀ alkenyl aryl group;
R ² for H, C ₁ -C ₁₆ alkyl, C ₂ -C ₁₈ alkenyl, C ₄ -C ₁₈ cycloalkyl, C ₁ -C ₁₈ alkyl aryl, C ₂ -C ₁₈ alkenyl aryl, hydroxy -C ₁ -C ₁₈ alkyl, a poly (oxyalkyl), polyalkylene polyamine or polyalkylene imine radical;
R ¹ and R ² together with the nitrogen atom to which they are attached optionally form a heterocyclic ring having 6 to 400 carbon atoms; and
R ^{3 stands} for an acyl residue of a mono- or polycarboxylic acid, and carries at least one free hydroxy and / or amino group, the amino group optionally carrying at least one hydroxy-C ₁ -C ₄ -alkyl group. 2. A compound according to claim 1, characterized in that R ^{3 is} an acyl radical of the formula (C = O) R ⁴ , in which R ⁴ is selected from C ₁ -C ₁₈ alkyl, C ₂ -C ₁₈ Alkenyl, C ₄ -C ₁₈ cycloalkyl, C ₁ -C ₁₈ alkyl aryl or C ₂ -C ₁₈ alkenyl aryl radicals which carry at least one hydroxyl group and / or amino group, and the analogues of these groups which carry at least one further carboxy group. 3. Compound according to one of the preceding claims, characterized in that R ^{1 is derived} from a poly-C ₂ -C ₆ alkene. 4. A compound according to claim 3, characterized in that the poly-C ₂ -C ₆ alkene is composed of monomers selected from ethylene, propylene, 1-butylene, i-butylene, 2-butylene or mixtures thereof. 5. A compound according to claim 4, characterized in that the poly-C ₂ -C ₆ alkene is a reactive poly-C ₂ -C ₆ alkene with a high proportion of terminal vinylidene groups. 6. A compound according to any one of the preceding claims, characterized in that R ^{1 represents} a C ₃₁ -C ₄₀₀ alkyl or alkenyl group; R ^{2 represents} H; and R ^{3 represents} an acyl residue of a mono- or polycarboxylic acid, selected from glyceric acid, gluconic acid, lactic acid, 2,2-dihydroxymethylpropionic acid and glutamic acid. 7. Water-in-fuel emulsion, characterized in that it contains as emulsifier at least one compound according to one of claims 1 to 6 in a proportion of about 1 to 20 wt .-%, based on the total weight of the composition, wherein R ¹ in compounds of the formula I can also represent a C ₆ -C ₃₀ alkyl or alkenyl group; optionally in combination with at least one other conventional emulsifier. 6. Water-in-fuel emulsion according to claim 7, characterized ge indicates that it also has about 60 to 95 wt% strength contains material and about 3 to 35 wt .-% water. 9. liquid explosive composition, characterized in that it comprises, as an emulsifier, at least one compound of the formula I according to any one of claims 1 to 6, optionally in combination with at least one further conventional emulsifier, wherein R ¹ in compounds of the formula I also can represent a C ₆ -C ₃₀ alkyl or alkenyl group. 10. A liquid explosive composition according to claim 9, characterized in that it comprises:

• a) 0.5 to 20% by weight of emulsifier of the formula I, where R ¹ in compounds of the formula I can also represent a C ₆ -C ₃₀ -alkyl or -alkenyl group;
• b) 2 to 20% by weight of an oil-immiscible, water-immiscible organic liquid;
• c) 2 to 30 wt .-% water and / or at least one water-miscible organic liquid;
• d) 40 to 90% by weight of an inorganic oxidizing agent;
• e) 0 to 25% by weight of customary other explosive additives, such as density-adjusting agents, combustible inorganic or organic solids.

11. Process for making a liquid explosive assembly Settlement according to one of claims 10 and 11, characterized records that the emulsifier of the formula I in a Oil phase forming organic liquid dissolves the organi cal solution heated if necessary and in it a given  if heated aqueous phase emulsifies which an inorganic includes oxidizing agent. 12. Fuel composition containing egg in a major amount nes hydrocarbon fuel protects against wear zende and / or corrosion inhibiting and / or as a detergent additive-acting amount of at least one compound of the general my formula I according to one of claims 1 to 6. 13. Lubricant composition containing a major amount of a liquid, semi-solid or solid lubricant effective amount of at least one compound of the general Formula I according to one of claims 1 to 6. 14. Fuel additive package containing in addition to conventional fuel additive at least one connection according to one of the claims che 1 to 6. 15. Use of a compound of formula I as defined in claim 1, as an emulsifier for liquid explosives, where R ¹ in compounds of formula I can also represent a C ₆ -C ₃₀ alkyl or alkenyl group. 16. Use of a compound of formula I as defined in claim 1 for water-in-fuel emulsions, as Ver anti-wear additive, anti-corrosion additive or detergent additive in hydrocarbon fuels and / or lubricants substances or as a corrosion-inhibiting additive in aqueous Liquids. 17. A process for the preparation of a compound of formula I according to claim 1, characterized in that an amine of For mel II
R ¹ R ² NH (II)
wherein R ¹ and R ^{2 have} the meanings given above, with a compound of the formula (III)
X (C = O) R ⁴ (III)
wherein (C = O) R ^{4 has} the meanings given for R ³ , and X stands for OH, halogen, OC ₁ -C ₆ alkyl, or O (C = O) R ^4a , where (C = O) R ^4a has the meanings given for R ³ or represents the remainder of a mono- or polycarboxylic acid.